#27 Ken Woodward: A Fork, A Precipice, A Decision

Host Ken Woodward shares a personal and professional dilemma faced upon receiving an unexpected resignation offer from his government employer. Reflecting on extensive conversations and internal contemplation, Ken explores the strengths and vulnerabilities of his situation.

Highlighting the obstacles and emotional turmoil faced while deciding to stay the course or resign, Ken raises numerous thought-provoking questions and discusses the considerations influencing his final decision. Through analyzing the risks and rewards, Ken aims to inspire others to leverage questioning for personal growth and decision-making even in uncertain times.

#26 Chad Littlefield: The Catalyst for Collaborative Conversations

Chad Littlefield is the co-founder and Chief Experience Officer of We and Me (www.weand.me). The organization aims to help leaders, educators, and events make connection easy. His successful 2015 Kickstarter for We! Connect Cards: Create Conversations that Matter, which is comprised of cards with questions on the front and a stretch on the back intended to make conversations fun and meaningful. Forbes calls Chad a “global expert on asking questions that build trust and connection in teams.” He is a TEDx speaker, bestselling author, and creator of Connection Toolkit™, which is now being used to create conversations that matter on campuses and companies in over 80 countries worldwide.

Chad and his late partner Will Wise launched their books How to Make Virtual Engagement Easy and Ask Powerful Questions: Create Conversations that Matter, both #1 Amazon Bestsellers. Chad's YouTube channel has over a million views, and he hosts the annual Connectors Summit in December to bring people together to hone their skills and meet like-minded people leading the vital work of connecting. He lives and delivers the enthusiasm you expect for someone trying to change the world through intentional connection.

The conversation delves into the transformative power of asking meaningful questions and building connections. Chad shares his journey of discovering the impact of questions, We Connect Cards' origin, and intention's role in effective questioning. The discussions also explore practical strategies for fostering deep connections and the societal impact of genuine curiosity. Full of insights and practical advice, this episode is a must-listen for anyone interested in enhancing their communicative skills and fostering stronger relationships.

#25 Seth Godin: Embracing Tension & Unleashing Questions Strategic Potential

Seth Godin is a bestselling author of 22 books in 39 languages, entrepreneur, and speaker. In April of 2025, he will upload his 10,000th daily blog post to one of the most popular blogs in the world; yeah, that's over 27 years of daily writing. Seth founded Squidoo and Yoyodyne (acquired by Yahoo!) and is credited as the inventor of email marketing (the good kind).

Seth has given five TED talks, including two that rank as the most popular of all time. By teaching about everything from effective marketing and leadership to the spread of ideas and our responsibilities as leaders, Seth has motivated and inspired people worldwide.

The conversation delves into Seth's background, achievements, and philosophy behind the power of asking questions. They discuss how questions can create tension, drive more profound understanding, and foster meaningful connections. Seth shares anecdotes from his experiences, offering practical examples of strategically using questions in various contexts, from personal interactions to professional settings.

The episode underscores the necessity of intentionality in asking questions to effect change, highlighting the strategic importance of inquiry in personal growth and leadership. It concludes with reflections on empathy, systemic challenges, and the enduring significance of caring and trying to make a difference, no matter the state of the world.

#24 Ken Woodward: Impactful Questions: Are You Better Off...

This episode dives into the significant political question posed by Ronald Reagan during the closing moments of his 1980 presidential debate with Jimmy Carter: 'Are you better off than you were four years ago?'

Ken Woodward explores the context of the 1980 political climate, marked by economic difficulties, high inflation, unemployment, and international issues such as the Iran hostage crisis and concerns about U.S. global standing and nuclear threats. Reagan's question, which became iconic in U.S. political discourse, was noted for its simplicity, personal relevance, emotional resonance, and strategic timing. The question invited voters to reflect on their circumstances rather than abstract policies, ultimately contributing to Reagan's landslide victory.

The episode details six crucial lessons for crafting influential questions, emphasizing audience perspective, engagement, simplicity, timing, self-reflection, and a call to action. Listeners are encouraged to consider how such questions have shaped their decisions and to apply these insights in personal and professional contexts.

#23 Ken Woodward: Right Now Questions Explored

This episode explores 'Right Now Questions,' a concept introduced in an earlier 2024 podcast episode. The episode compiles various interviews where individuals share their current pressing questions.

Featured guests include author Chazz Scott, who discusses life post-book release and physical recovery, and sisters Shreyaa and Esha Venkat from the nonprofit NEST4US, who are considering their future plans and educational transitions. Other contributors include educator Kwame Sarfo-Mensah reflecting on his roles, business leader Bill Reed sharing deep questions on emotional triggers and passions, and multi-hyphenate EbonyJanice Moore contemplating her priesthood journey. Art Historian and problem solver Amy Herman ties in personal and professional life experiences, and Executive Coach Jerry Colonna speaks on his transitional stage. The audience is invited to share their own Right Now Questions, fostering a continuous journey of learning and inspiration.

#22 Ken Woodward: 2024 Recap, Reflections, and A Look Ahead

This episode features a solo reflection by Ken Woodward, the host of the Curated Questions podcast, on episodes from 2024. Ken provides an overview and insights from 19 different episodes. Snapshots include significant points, questions, and background with various guests, including activists, authors, executives, and performers. Topics range from personal growth, mentorship, and identity to end-of-life reflections, historical contexts, and the use of questions in different facets of life. The episode note ends with a call for listener feedback and plans for improvements in 2025, emphasizing community growth and listener engagement.

#21 Shreyaa & Esha Venkat: A Clarion Call For Kindness & Social Good!

Sisters Shreyaa and Esha Venkat discuss the challenges they faced as young activists, the importance of asking questions, and their efforts to expand the nonprofit's impact both locally and globally. The conversation also touches on their personal development, the significance of self-care, and how community service has shaped their lives. Shreyaa and Esha emphasize the importance of involving young people in sustainable development and the power of simple acts of kindness. The episode encourages listeners to consider how they can make a difference in their communities and impact the world positively. Listen in for lots of questions!

#20 EbonyJanice Moore: A Benediction For Black Womanhood And Softness!

EbonyJanice recounts how her grandmother taught her to question texts early on. She shares insights from her spiritual mentorship program, 'Dream Yourself Free', and discusses her book 'All the Black Girls Are Activists' which delves into Black women's pursuit of dreams as resistance. EbonyJanice elaborates on the power of dreaming from a place of safety rather than resistance and the impact of nurturing Black women in her community. The discussion touches on societal pressures, systemic inequities, and the potential for transformative change when Black women are listened to and supported.

#19 Jerry Colonna: A Courageous Quest For Beloved Community

Through sharing personal stories, Jerry delves into the impact of his childhood, his experiences with depression, and his path to becoming a reporter who asked probing questions and tackling subjects that elicited deep emotional responses from business executives. He also discusses historical contexts and systemic issues stemming from fear and curiosity. Additionally, Jerry discusses the importance of remembering and acknowledging personal and communal histories to build better futures. The conversation is rich with insights into how powerful questions foster growth, belonging, and a deeper understanding of oneself and the world.

#18 Joe Primo: A Throughline: Death, Grief, Gratitude, And Grateful Living

Joe recounts his early experiences as a hospice chaplain, highlighting the importance of asking well-crafted, intentional questions to connect with and support grieving individuals. He emphasizes the foundational role of gratefulness in discovering meaning in life and shares stories from his work with children and families facing death. Joe discusses how grief, while universal and normal, is often mishandled due to societal discomfort and lack of understanding. He urges listeners to acknowledge, embrace, and integrate grief to move forward healthily. The conversation also delves into the commercialization of gratitude and how to return to its core essence as a spiritual practice. The episode concludes with Joe's reflections on living a grateful life, making improbable friends, and asking courageous questions to foster deeper understanding and connections.

#17 Amy Herman: Art And Inquiry As A Threshold To Our Humanity

Amy shares her experiences from law and art history, emphasizing how questioning can broaden knowledge and improve problem-solving skills. Additionally, her expertise underscores the significance of effective communication, human connections, and shared experiences across personal and professional contexts. The conversation touches on themes of situational awareness, self-reflection, and the growth that comes from embracing imperfections, drawing on real-life examples and anecdotes, like learning from a retired prison guard and understanding trauma through the art of kintsugi.

#16 Chazz Scott: Mental Conditioning & The Path To Self-Discovery

Chazz shares his journey of self-discovery, catalyzed by reading 'The Power of Positive Thinking' and how this led him to establish nonprofit Positively Caviar, focusing on youth mental health resilience. Chazz emphasizes the role of questions in understanding oneself and shaping one’s destiny. He discusses how his personal struggles, including overcoming a significant injury, have informed his approach to self-care and mental wellness. The conversation covers the importance of slowing down, being inquisitive, and developing morning routines as pathways to living authentically. Chazz highlights how empowering questions and self-inquiry can alter our perspectives and enhance our lives.

#15 Kwame Sarfo-Mensah: The Vocabulary of Identity & Creating Culturally Affirming Classrooms

Kwame explores the concept of identity, including personal and social identities, and how these can affect one's experience in the world. The conversation delves into the challenges of addressing identity in educational settings and the importance of diversity, equity, inclusion, and accessibility. Kwame shares his experiences and insights on the power of questions in navigating contract negotiations, understanding student backgrounds, and self-growth. The dialogue also touches on unlearning ingrained biases and recognizing privileges. The discussion concludes by reflecting on the role of questions in fostering a more inclusive and understanding society.

#14 Bill Reed: Questions At The Heart Of Leadership, Mentorship and Relationships

The discussion delves into how questions have shaped Bill’s parenting, leadership, and mentoring approach, emphasizing the importance of curiosity and intentional relationship-building. We also explore the impact of effective questioning in meetings and mentoring relationships, focusing on Bill's current endeavors and insights into fostering a culture of transparency and authentic inquiry.

#13 David Pearl: Questions As A Creative Force At The Intersection Of Curiosity, Business, And Art

The conversation highlights Pearl's journey from his early musical career to pioneering 'experience engineering' and founding the initiative Street Wisdom. Key themes include the transformative power of questioning, the resilience of a playful mindset, and the importance of curiosity in both personal and professional realms. Additionally, we delve into meaningful connections through shared interests and reflective walks, emphasizing how profound questions can build understanding, community, and personal development. The discussion underscores re-evaluating work and life's purpose, creativity, imagination, and the complexities of human interaction.

#12 Jimmy D. Smith: Navigating Leadership, Friction, Mentorship, and Legacy

Smith shares his inspiring career journey from an aspiring pilot to a guardian of the nation's nuclear arsenal, highlighting the importance of persistent inquiry, mentorship, and community engagement. He discusses his unique work habits and strategies for career advancement and introduces the 'Talk Backwards' methodology for relationship building. Smith also emphasizes selflessness, integrity, and his initiatives in STEM programs, particularly with HBCUs, providing scholarships, internships, and job opportunities. Personal anecdotes and life lessons from his mentor, Vice Admiral Paul Sullivan, are woven throughout, encouraging listeners to question, grow, and help others succeed.

#11 Cal Fussman: A Storyteller's Quest for Connection & Belonging

Cal shares anecdotes from his experiences, such as the impact of writing to President Lyndon B. Johnson at seven, his path through journalism school, and his unique interviewing style that emphasizes curiosity and connection. From interviewing world leaders and celebrities to teaching corporate workshops on communication, Cal explains how thoughtful questioning can build trust, foster belonging, and elicit profound insights. He also reflects on his travels and the importance of understanding core human stories. The conversation underscores the transformative power of questions in shaping lives and careers.

#10 Nikki Giovanni: Reflections On Life, Galaxies, & A Poetic Exploration of Questions

The conversation explores Nikki's reflections on the significance of the power of words, influential librarians, and growing up Black in America. Giovanni shares impactful moments and discusses age, curiosity, societal challenges, and learning philosophies. The dialogue delves into her deep understanding of history, human nature, black women's significance, and space exploration. Giovanni's personal anecdotes and poems provide a rich narrative on societal issues, the beauty of nature, joy, curiosity, and the importance of chosen relationships over familial ties.

#09 Derek Sivers: Challenging Conventions, Reframing, & The Intentional Path

Derek delves into his experiences with questioning assumptions, pushing boundaries, and the role of journaling for self-reflection. The conversation encompasses topics like the importance of reframing perspectives, cultural differences in questioning, and Sivers' embrace of minimalism. He advocates for reframing situations and adopting beliefs that are useful over what is "true." Practical advice and anecdotes underscore the value of curiosity and inquiry, offering valuable insights into leading a more examined life through the transformative power of questions.

#08 Brian Fretwell: Finding Good, Fighting Loneliness, and Embracing Self-Interested Curiosity

Brian weaves together how neuroscience, community, and our stories form the bonds of connection with those we choose to engage. During a portion of the conversation, he uses the Success Mapping framework to understand Ken's motivation for this podcast. He then introduces the 'blueberries' analogy, a metaphor for personal experiences, and explains how genuine curiosity about these experiences is critical to real connection and a path toward addressing loneliness.